The Magnificent Seven: The Top 7 Undertaker Main Event Matches

The Undertaker was one of the longest standing WWE stars of all time. It’s telling that he worked his first main event match at the This Tuesday in Texas show in 1991, and that his (presumptive) last match was a main event over twenty five years later at WrestleMania 33.

In between these matches, The Undertaker worked quite a few main events, and many of them much better than his first and last efforts. So, this column looks at the seven best main event matches The Undertaker was involved in. I opted to limit the list to one-on-one main event matches—in particular to rule out The Dead Man’s many appearances in Royal Rumble matches that might have threatened to overtake the countdown. Moreover, I only counted main events in the sense of the last match of the card, not other matches WWE may have billed as additional main events on a loaded card.

This countdown is based on match quality alone; while the preceding storyline and, at times, the aftermath inevitably plays a role in how a match is received, the focus was on the match in and of itself rather than any surrounding factors.

#7. Brock Lesnar, SummerSlam 2015

Battleground 2015 saw a memorable main event scene. Brock Lesnar largely dominated WWE Champion Seth Rollins in an entertaining romp, but before he could finish off The Architect, The Undertaker made a surprise return to cost Lesnar the title. The next night on Raw, things got even better, with The Undertaker and Lesnar in a pull-apart brawl.

SummerSlam saw the collision beween these two larger than life stars in the match that their WrestleMania 30 showdown probably should have been—a stiff, violent brawl. While some fans balk at the finish, it fit the story of this rivalry perfectly. The Undertaker was desperate to avenge Lesnar ending his WrestleMania undefeated streak, and realized he might be outgunned, so he resorted to desperate measures. So there was the false finish of The Undertaker tapping out so Lesnar would let him out of kimura, but not so the referee would see. From there, The Phenom nailed a low blow and locked in Hell’s Gate to choke him out. Intense and defiant to the end, Lesnar gave his opponent the finger even as he faded out of consciousness. No, the match wasn’t conclusive and set up their Hell in a Cell match to follow, but it was entertaining in and of itself and quite arguably the best match in a catalog of very good encounters between the two.

#6. Edge, One Night Stand 2008

From 2007 through much of 2008, The Undertaker and Edge engaged in a terrific feud, chock full of excellent specialty matches. Their TLC war at One Night Stand 2008 was one of their finest exhibitions—a violent match with the built in story that this time The Phenom was the underdog, fighting Edge in his signature match, and a match that invited La Familia to get involved.

While some favor the WrestleMania 24 main event match over this one, and I agree that one was great and probably better from a purist’s perspective, I loved the carnage of this outing as The Undertaker fended off The Edgeheads, Chavo Guerrero, and Bam Neeley before finally succumbing to The Rated Edge Superstar tipping him of a ladder and through a series of tables, for Edge to finally steal back his the World Heavyweight Championship.

#5. Bret Hart, SummerSlam 1997

It’s easy to forget that, on the early end of the Attitude Era, Bret Hart was a major player, and his heel turn and Hart Foundation stable were outstanding early rivals for Steve Austin as he morphed into an anti-hero, and before he got to really feuding with Vince McMahon. Similarly, The Undertaker is remembered in this period as Biker ‘Taker or for his dark turn as the leader of the Ministry of Darkness prior to that. Before those gimmick shifts, he was more or less the same character he’d played since 1990, albeit with a bit more edge and fire.

And so, for SummerSlam 1997, the two were set on a collision course, with the added intrigue of Shawn Michaels playing guest referee. HBK was already a kayfabe and real life bitter rival to Hart. He and The Dead Man weren’t allied with one another, but there was rather a shade of gray around him being the face and the WWF Champion sandwiched between two heels going to war. As additional layers, Hart vowed never to wrestle in the US again if he lost, while Michaels had to agree to the same if he didn’t call the match down the middle.

Hart and The Undertaker had had very good matches before, but the added elements of Hart working heel, and the heat HBK added, not to mention a half hour for the guys to work with, elevated the bout to an instant classic. Best of all was the iconic finish that saw Hart spit on Michaels and Michaels respond by swinging a chair at him, only to accidentally nail The Undertaker, only to be completely impotent to do anything but count the pin fall, even though it gave his arch-rival the world title and gave Michaels a new dangerous enemy in The Dead Man.

#4. Shawn Michaels, WrestleMania 26

The Undertaker and Shawn Michaels may have seemed like unlikely rivals for their different styles, and yet the two created magic together when they got in the ring. That’s particularly true of their WrestleMania 25 classic, on the short list for the greatest match either man ever had, and for the greatest match in WrestleMania history. One year later, Michaels goaded The Phenom into a rematch. The Undertaker put his undefeated streak on the line against his most talented rival. And Michaels? He promised to retire if he lost.

While I’m in the camp that feels this match fell short of its predecessor a year earlier, it was nonetheless a great match, and an all time great WrestleMania main event. These guys were good enough that, even their third best match (we’ll get to #2 in my book…) was still a rock solid four-and-a-half-star-ish encounter. After twenty four minutes of tremendous back and forth action, it all came down to Michaels, reverting to his rebellious old self as he struggled to his feet and mimicked The Undertaker’s coat-throat taunt. A moment later, he he ate an especially vicious jumping Tombstone—the final exclamation point at the end of a remarkable career.

#3. Kurt Angle, No Way Out 2006

For all of the iconic matches both The Undertaker and Kurt Angle have each had, this one tends to get forgotten for falling well after the Attitude Era and at a B-PPV, when The Undertaker was largely a filler challenger to get Kurt Angle to WrestleMania. The reality of the situation is, however, that this match may very well have represented two all time greats at or around their primes as in-ring performers.

This match was the story of Angle as an elite athlete battling The Undertaker as an unstoppable force. They waged war for half an hour, culminating in trading finishers before Angle escaped a choke by rolling up The Dead Man to steal the pin. While some could call the finish cheap for the flash pin scenario, it also highlighted the differences between the two—The Undertaker was out for destruction while, at least for that night, Angle was the better pure wrestler who never took his eyes off of winning the match.

#2. Edge, SummerSlam 2008

I get that this isn’t everyone’s favorite Undertaker-Edge match, but it was mine. I’d label it the best Hell in a Cell match without any big falls off the cage, nor blood. It was good, intense brawl, and I loved the change in dynamics for this finale to the Undertaker-Edge feud. Up to this point, the story was that Edge was a great wrestler, but also a conniving, scared heel looking to manipulate his way into a victory or retaining his title. In this blow off match, there was no title on the line, but rather just the final encounter to cap a great rivalry. Moreover, Edge flipped the switch after brutalizing Mick Foley on Smackdown to go from intimidated to crazed and determined to win. This one largely saw Edge as the aggressor, but nonetheless ultimately unable to overcome The Dead Man.

While I get the criticism that this one was a bit of a spotfest, and, again, will agree that the WrestleMania 24 was at least on par if not better from a purist’s perspective, I loved the poeticism of this match in particular as chairs and video cameras and a ladder came into play, recalling many of the best moments of the rivalry leading up to this match, before The Undertaker hit one last Tombstone for the pin, followed by one last chokeslam off of a ladder and through the mat to decisively win the feud.

#1. Shawn Michaels, Badd Blood 1997

There’s a reason Hell in a Cell is still so over as a gimmick match. Some of it has to do with the sheer immensity of the structure and history of falls off the top or high on the sides of the cage. Some if is a history of good to great matches. And then there’s the original Cell match. Shawn Michaels. The Undertaker. The early days of the Attitude Era and a deeply personal beef.

The Michaels-Undertaker issue of 1997 started with Michaels accidentally walloping The Dead Man with a chair to cost him his WWF Chamionship at SummerSlam. Things built up with Michaels playing the perfect jerk and surrounding himself with the first iteration of DX to defend him. The Cell was the proper way to blow off their issue in an intense environment that would lock out Michaels’ helpers.

The match to follow encapsulated a lot of what’s great about Michaels and The Undertaker respectively. Michaels had the opportunity to show his fire in standing toe to toe with a much larger opponent, but also sell his ass off like he really was getting destroyed. Meanwhile, the Cell was the perfect environment for The Undertaker to come across as an unstoppable force as just kept coming with the heavy artillery.

While some might balk at the finish to this match for being a bit of schmozz, it worked beautifully in its context for Kane to appear and cost his brother the match. The finish protected Michaels as he geared up for another world title reign, while also protecting The Phenom from absorbing a real loss.

Meanwhile, the fans got the electricity of Kane finally debuting. The debut itself was fantastic for the sight of him ripping the door off the Cell and destroying The Dead Man, setting in motion their own program to extend over months (and, off and on, years) to follow.

The Undertaker has had some great main event matches, but there are many ways in which this may have been the most influential, the most violent, and truly one of the best.

Which matches would you add to the list? My top honorable mentions included his main events opposite Batista (Survivor Series 2007), Edge (WrestleMania 24), and Steve Austin (SummerSlam 1998). Let us know what you think in the comments.

Read more from Mike Chin at his website and follow him on Twitter @miketchin.